Amine salts of aromatic sulphonic acids



Patented Sept. 1, 1936 UNITED STATES AMINE SALTS OF AROMATIC SULPHONICACIDS George R. Tucker, North Andover, Mass" asaignor to Dewey and AlmyChemical Compa y. North Cambridge, Mass., a corporation of MassachusettsNo Drawing. Application July 3. 1933.

Serial No. 679.004

7 Claims. (Cl. 280129) This invention relates to new naphthalenederivatives and particularly to the class of compounds prepared byneutralizing either monoor further substituted sulphonic acids withhydroxyalkyl amines. Such compounds find special use as addition agentsin hydraulic cement.

One class of compounds (so classified because it is particularlyvaluable for the manufacture of cellular concrete products) may beprepared by condensing aliphatic alcohols such as iso-propyl or n-butylalcohol with a naphthalene sulphonic in the presence of a suitabledehydrating agent.

Members of the second group, serviceable to improve the plasticity ofthe wet concrete and the strength of hardened concrete may be preparedby condensing an aromatic sulphonic acid with formaldehyde or itsequivalent and are believed to be sulphonic acids of polymerizedhydrocarbons or derivatives thereof having two or more aromatic nucleijoined to a methylene group or a single carbon atom.

It is the purpose of this invention to produce hydroxy-alkyl amine saltsof the above compounds. Hydroxyalkylamine salts of sulphonic acidschosen from either of the described groups may be made by neutralizingthe chosen acid either partially or completely with thehydroxyalkylamine.

The preferred control is to titrate a sample of the pure naphthalenesulphonic acid from either 'of the above groups with sodium hydroxideuntil it is just blue to litmus and therefrom to obtain the factor forthe hydroxyalkylamine, for example, triethanol amine.

Since the molecules of the formaldehyde condensed sulphonic acids alwayscontain at least two SOs-H groups, a series of salts may be formed fromthese acids by the substitution of one or more of the replaceablehydrogen atoms. In the simplest instance, one half of the amount of thehydroxy-alkyl amine required to neutralize completely the sulphonic acidmaybe added, thus producing the acid salt. Again 1 mol. of sodiumhydroxide or other suitable alkali and 1 mol. of thehydroxy-allgvl-amine may be added, forming a sodium amine salt, or thereplaceable hyrogen atoms may be completely replaced by the amine alone.

Empirical examples follow.

Example 1 To the quantity of a given pure condensed sulphonic acid from1000 lbs. naphthalene prepared as set forth in my application for U. S.patent, Serial No. 643,741, filed November 21, 1932, add puretriethanolamine or a lesser quantity of the commercial grade oftriethanolamine to complete neutralization.

Example 2 To a given quantity of n-butyl naphthalene sulphonic acid addpure triethanolamine or a lesser quantity of the commercial product tocomplete neutralization.

Example 3 To a given quantity of iso-propyl naphthalene sulphonic acidadd pure triethanolamine or a lesser quantity of the commercial product.

Example 4 To a given quantity of the pure condensed sulphonic acid fromnaphthalene prepared as set forth in my application for U. S. patent,Serial No. 643,741,'flled November 21, 1932, add an amount oftriethanolamine to replace the hydrogen in substantially one-half of thesulphonic acid groups and an amount of sodium hydroxide or an equivalentquantity of other alkali to replace the hydrogen ln the remainingsulphonic acid. The solutlons may be evaporated to give the dry salts-orused in water solution.

In place of naphthalene in the foregoing sulphonation and condensationprocedure may be employed any aromatic hydrocarbon such as benzene,diphenyl, anthracene, phenanthrene, fluorene, etc., or any homologue orderivative thereof, as set forth in my aforesaid application.

1 claim:

1. A hydroxy-allayl amine salt of a lower alkylated naphthalenesulphonic acid.

2. A hydroxy-alkyl amine salt of the formaldehyde condensation productof an aromatic sulphonic acid.

3. A triethanolamine salt of the formaldehyde condensation product ofbeta naphthalene sulphonic acid.

4. A salt having the general formula Rr-SO3X in which R indicates anaphthalene group and X an alkylol amine.

5. A salt having the general formula GEORGE R. TUCKER.

